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Does 2-Methylacetophenone Comply with Steric Inhibition of Resonance? A Direct Experimental Proof of Its Nonplanar Conformation from a Joint Ab Initio/Electron Diffraction Analysis
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SYSNO ASEP 0355541 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Does 2-Methylacetophenone Comply with Steric Inhibition of Resonance? A Direct Experimental Proof of Its Nonplanar Conformation from a Joint Ab Initio/Electron Diffraction Analysis Author(s) Hnyk, Drahomír (UACH-T) SAI, RID, ORCID
Samdal, S. (NO)
Exner, Otto (UOCHB-X)
Wann, D. A. (GB)
Rankin, D. W. H. (GB)Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 75, č. 15 (2010), s. 4939-4943Number of pages 5 s. Language eng - English Country US - United States Keywords substituted benzoic-acids ; nuclear-magnetic-resonance ; gas-phase Subject RIV CA - Inorganic Chemistry CEZ AV0Z40320502 - UACH-T (2005-2011) AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000280398100006 DOI 10.1021/jo100291r Annotation The GED results, supported by the calculations that involve long-range correlation, are in a good agreement with C-13 NMR spectroscopic investigations, UV spectra, and dipole moment studies. However, previous claims that assumed steric inhibition of resonance caused by a significantly nonplanar conformation with phi close to 90 degrees have been disproved. Steric crowding is evident from the geometrical parameters, particularly from the C(1)-C(2) bond length and from the C(1)-C(2)-C(H-3) and C(2)-C(1)-C(O) bond angles. It is concluded that any explanation of reactivity by steric inhibition of resonance and by other steric factors must be supported by experimental and/or theoretical investigation of the actual molecular shape. Workplace Institute of Inorganic Chemistry Contact Jana Kroneislová, krone@iic.cas.cz, Tel.: 311 236 931 Year of Publishing 2011
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